Sodium Carbonate → 6-(4-morpholinyl)-3,4-dihydro-2H-1,4-benzothiazine 1,1-dioxide

HRID 1618644Notes

Reaction equation

HRID 1618644 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].C([N:10]1[C:15]2[CH:16]=[C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH:18]=[CH:19][C:14]=2[S:13](=[O:27])(=[O:26])[CH2:12][CH2:11]1)(=O)C.[OH-].[K+]>CO.O>[N:20]1([C:17]2[CH:18]=[CH:19][C:14]3[S:13](=[O:27])(=[O:26])[CH2:12][CH2:11][NH:10][C:15]=3[CH:16]=2)[CH2:21][CH2:22][O:23][CH2:24][CH2:25]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 14797Potassium HydroxideHCID 672864174-acetyl-6-morpholin-4-yl-3,4-dihydro-2H-1,4-benzothiazine 1,1-dioxide

Product 1

HCID 672847356-(4-morpholinyl)-3,4-dihydro-2H-1,4-benzothiazine 1,1-dioxide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-acetyl-3,4-dihydro-2H-1,4-benzothiazin-6-amine 1,1-dioxide 2-bromo ethyl ether (1.276 g, 5.5 mmol) and sodium carbonate (1.06 g, 10 mmol) in MeOH (5 mL) was stirred at 150° C. for 1.5 h. After this time the reaction mixture was cooled to rt and LCMS shows intermediate 4-acetyl-6-morpholin-4-yl-3,4-dihydro-2H-1,4-benzothiazine 1,1-dioxide. The compound was suspended in 3.5 mL of water and treated with KOH (1.82 g, 32.5 mmol) and the resulting mixture was stirred at 55° C. for 1 h. After this time the reaction was cooled and the resulting precipitate was filtered to give 6-morpholin-4-yl-3,4-dihydro-2H-1,4-benzothiazine 1,1-dioxide as white solid. Mass Spectrum (ESI) m/e=269 (M+1).

Workup

  1. temperatureAfter this time the reaction was cooled
  2. filtrationthe resulting precipitate was filtered

Sources & evidence

ORD record
ord-f20947077b0c479bb191ec3af96b9534
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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